Nitrone [2+3]-Cycloadditions in Stereocontrolled Synthesis of a Potent Proteasome Inhibitor:  (−)-Omuralide

Abstract

A new stereocontrolled synthetic route to omuralide has been developed from methyl pyroglutamate. This route involves regio- and stereoselective N-methylnitrone 1,3-dipolar cycloadditions to appropriate pyrrolinones, beta-eliminations, and highly selective hydrogenations as the main steps.